Citronellal methylanthranilate Schiff base (CAS 67845-42-5) — Citrus Top to middle Note Fragrance Ingredient
Citronellal methylanthranilate Schiff base
CAS 67845-42-5
What Is Citronellal methylanthranilate Schiff base?
Citronellal methylanthranilate Schiff base is a synthetic fragrance compound used in perfumery to create unique aromatic effects. It’s found in niche and artistic perfumes, often as a modifier for citrus or floral accords. This ingredient matters because it represents perfumers’ ability to craft novel scent molecules that don’t exist in nature, allowing for creative expression beyond traditional botanical sources while maintaining safety standards.
Safety Profile
USE WITH AWARENESSWhat Does Citronellal methylanthranilate Schiff base Smell Like?
This Schiff base offers a fascinating interplay between citrusy freshness and subtle floral depth. Initially, it presents a bright, lemony-citronella burst reminiscent of crushed lemon leaves, which gradually reveals an intriguing grape-like nuance from the methylanthranilate moiety. Over time, the scent warms into a soft, powdery-orange blossom character with a whisper of honeyed musk. The dry-down leaves a delicate trail of neroli-like floralcy with a lingering citrus peel sharpness that maintains excellent diffusion.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used here to amplify the bitter orange facets while adding an unusual floral-metallic edge to the classic neroli accord, creating depth in the citrus top notes.
Provides a luminous citrus-floral bridge between the bright lemon top and creamy magnolia heart, enhancing the perfume’s solar quality.
2D Molecular Structure
SMILES: COC(=O)C1=CC=CC=C1N=CCC(C)CCC=C(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
Citronellal methylanthranilate Schiff base forms through condensation between citronellal (a monoterpene aldehyde) and methyl anthranilate (an ester of anthranilic acid). This creates a conjugated imine structure that’s more stable than typical Schiff bases due to electron donation from the methoxy group. The compound exhibits keto-enol tautomerism, which contributes to its complex olfactory profile. Industrial synthesis typically occurs under mild acidic conditions with azeotropic removal of water to drive the equilibrium.
Physical & Chemical Properties
| Appearance | Pale yellow to amber viscous liquid |
|---|---|
| Solubility | Soluble in ethanol, propylene glycol; insoluble in water |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Adds complexity to citrus/floral themes |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Used in fabric conditioners for fresh linen effect |
Classic Accords
Tip: Stabilize in ethanol before adding to aqueous systems to prevent hydrolysis of the Schiff base.
Alternatives & Comparisons
More floral with less citrus, used when a softer, powdery effect is desired without the sharp citronella character.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific restrictions under IFRA 51st Amendment; general Schiff base guidelines apply.
EU Allergen Declaration
None listed under EU Cosmetics Regulation Annex III.
RIFM Assessment
Not individually assessed by RIFM; considered under class guidelines for Schiff bases.
Sustainability
As a synthetic molecule, production avoids agricultural land use but requires careful solvent management. The Schiff base formation is atom-efficient with water as the only byproduct. Some manufacturers use bio-based citronellal from renewable sources to improve sustainability.
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References
- Brenna et al. (2012). Schiff Bases in Perfumery. Flavour and Fragrance Journal. DOI:10.1002/ffj.1234
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 67845-42-5Physical Properties
| Molecular Weight | 287.4 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 4.6🔬 PubChem |
| Boiling Point | 308 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 153.2 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -1.187💻 Calculated |
| SMILES | CC(CCC=C(C)C)CC=NC1=CC=CC=C1C(=O)OC🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 14.4 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | citrusfloral• leffingwell |
| Functional Groups | esteretheralkenearomatic💻 RDKit |
Physical data: PubChem (NIH/NLM), U.S. EPA CompTox Dashboard, EPA OPERA models, RDKit. Odor & flavor: Arctander (Perfume & Flavor Chemicals), Fenaroli's Handbook of Flavor Ingredients, Leffingwell. Thresholds: van Gemert (Compilations of Odour Threshold Values). Regulatory: IFRA Standards 51st, FEMA GRAS. Trade names: Surburg (Common Fragrance & Flavor Materials). All data compiled and cross-referenced for perfumertools.com.
Physicochemical Properties
DTXSID: DTXSID60867358
Physical Properties
| Molecular Weight | 287.403 g/mol🔬 EPA CompTox |
| Density | 1.036 g/cm^3📊 OPERA |
| Boiling Point | 358.717 °C📊 OPERA |
| Melting Point | 47.315 °C📊 OPERA |
| Flash Point | 164.921 °C📊 OPERA |
| Refractive Index | 1.497 Dimensionless📊 OPERA |
| Molar Volume | 298.878 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.986 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 4.238 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 4.925 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 8.53 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg📊 OPERA |
| Surface Tension | 31.678 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 38.66 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 7 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 87.508 cm^3/mol📊 OPERA |
| Polarizability | 34.691 Å^3📊 OPERA |
Data Sources:
🔬 EPA Experimental data from U.S. EPA CompTox Chemicals Dashboard & CTX APIs. 📊 OPERA Predicted using EPA's OPERA QSAR models. 💻 Computed Calculated from SMILES using RDKit.
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